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Preparation method of 1-chloro-4-(6-nitrocyclohex-3-alkenyl)-benzene

A technology of nitrostyrene and cyclohexyl, which is applied in the field of organic compound synthesis, can solve the problems that cannot meet the actual requirements, and achieve the effects of shortening the synthesis time, mild synthesis conditions and improving the reactivity

Pending Publication Date: 2022-03-18
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, with the continuous increase in market demand for boscalid and the continuous improvement of the safety production requirements of chemical companies, the above-mentioned existing synthetic 1-chloro-4-(6-nitrocyclohex-3-ene base)-benzene method has been unable to meet the actual requirements

Method used

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  • Preparation method of 1-chloro-4-(6-nitrocyclohex-3-alkenyl)-benzene
  • Preparation method of 1-chloro-4-(6-nitrocyclohex-3-alkenyl)-benzene

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Effect test

Embodiment 1

[0022] A preparation method of 1-chloro-4-(6-nitrocyclohex-3-enyl)-benzene, comprising the following steps:

[0023] Under nitrogen protection, 112.4g (98%, 0.6mol) trans-4-chloro-β-nitrostyrene, 400g xylene, 0.33g (99%) anhydrous ZnCl 2 , after heating to 20°C, 39.1 g (99.9%, 0.72 mol) of 1,3-butadiene was introduced slowly, and the introduction of 1,3-butadiene was controlled for 4 hours to complete. After the reaction was completed, it was filtered, desolvated, and the residue was recrystallized from methanol, and dried under vacuum at 40°C to obtain 142.1 g of light yellow solid 1-chloro-4-(6-nitrocyclohex-3-enyl)-benzene with a content of 98.4 %, yield 98.1%. 1 H-NMR (500MHz, CD 2 Cl 2 ): δ=7.31-7.26(m, 2H), 7.21-7.16(m, 2H), 5.82-5.76(m, 1H), 5.74-5.69(m, 1H), 4.97-3.89(m, 1H), 3.42 -3.35 (m, 1H), 2.79-2.72 (m, 2H), 2.51-2.42 (m, 1H), 2.35-2.25 (m, 1H) ppm, proved the successful preparation of 1-chloro-4-(6-nitrate Cyclohex-3-enyl)-benzene.

Embodiment 2

[0029] A preparation method of 1-chloro-4-(6-nitrocyclohex-3-enyl)-benzene, comprising the following steps:

[0030] Under nitrogen protection, 112.4g (98%, 0.6mol) trans-4-chloro-β-nitrostyrene, 400g xylene, 0.33g (99%) anhydrous ZnCl 2 After heating to 40°C, 39 g (99.9%, 0.72 mol) of 1,3-butadiene was introduced slowly, and the introduction of 1,3-butadiene was controlled for 5 hours to complete. After the reaction was completed, it was filtered, desolvated, and the residue was recrystallized from methanol, and dried under vacuum at 40°C to obtain 141.4 g of light yellow solid 1-chloro-4-(6-nitrocyclohex-3-enyl)-benzene with a content of 98.6 %, yield 97.8%.

Embodiment 3

[0032] A preparation method of 1-chloro-4-(6-nitrocyclohex-3-enyl)-benzene, comprising the following steps:

[0033] Under nitrogen protection, 112.4g (98%, 0.6mol) trans-4-chloro-β-nitrostyrene, 400g xylene, 0.49g (99%) anhydrous ZnCl 2, after heating to 20°C, 39.1 g (99.9%, 0.72 mol) of 1,3-butadiene was introduced slowly, and the introduction of 1,3-butadiene was controlled for 4 hours to complete. After the reaction was completed, it was filtered, desolvated, and the residue was recrystallized from methanol, and dried under vacuum at 40°C to obtain 142.3 g of light yellow solid 1-chloro-4-(6-nitrocyclohex-3-enyl)-benzene with a content of 98.4 %, yield 98.2%.

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Abstract

The invention discloses a preparation method of 1-chloro-4-(6-nitrocyclohex-3-alkenyl)-benzene, which is characterized in that trans-4-chloro-beta-nitrostyrene and 1, 3-butadiene are used as reaction raw materials, and reaction is carried out under the condition that a catalyst is ZnCl2, so that the 1-chloro-4-(6-nitrocyclohex-3-alkenyl)-benzene is prepared. The preparation method of 1-chloro-4-(6-nitrocyclohex-3-alkenyl)-benzene has the advantages of low cost, mild reaction conditions, high reaction efficiency, high raw material utilization rate, high product yield, high product content and the like, and also has the advantages of simple process, easily available raw materials, suitability for large-scale production, facilitation of industrial application, high use value and good application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and relates to a preparation method of 1-chloro-4-(6-nitrocyclohex-3-enyl)-benzene. Background technique [0002] 1-Chloro-4-(6-nitrocyclohex-3-enyl)-benzene is an important intermediate in the synthesis of boscalid. The main downstream product, boscalid, is a new type of nicotinamide fungicide developed by BASF in Germany. The common name is boscalid, also known as nicobifen, and the test number is BAS510. Boscalid has been registered in 50 countries for the control of 80 diseases on 100 crops; several excellent boscalid compound preparations have been registered in China, such as Nopoxin Cuijia, Fenqiao, Ruidefeng Cuirun, etc. As the patent and administrative protection of boscalid have expired in many markets such as Europe, America and China, the peak sales target of more than 300 million euros will trigger many non-patented product manufacturers to participate in its mark...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/10
CPCC07C201/12C07C2601/16C07C205/10
Inventor 高云英罗先福干兴利王燕黄幼援朱银海臧阳陵杜升华
Owner HUNAN CHEM RES INST